Toluene → 2-Phenylthiomethyl-4-sec-butyl-6-methoxysaccharin

HRID 129053Notes

Reaction equation

HRID 129053 reaction equation
[CH:1]([C:5]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]2[C:6]=1[C:7](=[O:18])[NH:8][S:9]2(=[O:11])=[O:10])([CH2:3][CH3:4])[CH3:2].CC(C)([O-])C.[K+].C1([CH:31]([S:33]C(Cl)C2C=CC=CC=2)Cl)C=CC=CC=1.[C:42]1(C)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:42]1([S:33][CH2:31][N:8]2[C:7](=[O:18])[C:6]3[C:12](=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:5]=3[CH:1]([CH2:3][CH3:4])[CH3:2])[S:9]2(=[O:10])=[O:11])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 20138743Phenylchloromethyl sulfideHCID 23665647Potassium tert-butoxideHCID 677845614-Sec-butyl-6-methoxysaccharin

Product 1

HCID 677843062-Phenylthiomethyl-4-sec-butyl-6-methoxysaccharinYield 60%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 4-sec-butyl-6-methoxysaccharin (3 g), toluene, potassium t-butoxide (1.4 g), and tetrabutylammonium bromide (0.4 g) was brought to reflux and phenylchloromethyl sulfide (1.8 mL) was added. The reaction mixture was refluxed for about 27 hours, the solvent was removed in vacuo, the residue was extracted with ethyl acetate, washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane to afford 2.63 g (60%) of 2-phenylthiomethyl-4-sec-butyl-6-methoxysaccharin.

Workup

  1. temperatureto reflux
  2. temperatureThe reaction mixture was refluxed for about 27 hours
  3. customthe solvent was removed in vacuo
  4. extractionthe residue was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-84f738588e9e4ac995771c12a62e54f0
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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